Skip to main content
SpringerLink
Log in

A fluorescent probe for colorimetric detection of bisulfite and application in sugar and red wine

  • Published:
Food Science and Biotechnology Aims and scope Submit manuscript

Abstract

A new fluorescent probe made from (E)-2-(benzo[d]thiazol-2-yl)-3-(6-hydroxynaphthalen-2-yl) acrylonitrile (Probe 1) was synthesized for the determination of bisulfite concentrations in real food samples (red wine and sugar). Adding bisulfite to a Probe 1 solution caused a marked decrease in fluorescence intensity and a visual color change from yellow to light yellow. This distinct color response indicates that Probe 1 could be used as a visual sensor for bisulfite. Probe 1 can detect bisulfite quantitatively in the range 0–400 μM with a detection limit of 0.10 μM. This makes Probe 1 a convenient signaling instrument for determining bisulfite levels in sugar and red wine samples.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  • Chen S, Hou P, Wang J, Song X. A highly sulfite-selective ratiometric fluorescent probe based on ESIPT. RSC Adv. 2: 10869–10873 (2012)

    Article  CAS  Google Scholar 

  • Choi MG, Hwang J, Eor S, Chang SK. Chromogenic and fluorogenic signaling of sulfite by selective deprotection of resorufin levulinate. Org. Lett. 12: 5624–5627 (2010)

    Article  CAS  PubMed  Google Scholar 

  • Daunoravicius Z, Padarauskas A. Capillary electrophoretic determination of thiosulfate, sulfide and sulfite using in-capillary derivatization with iodine. ElectropHoresis 23: 2439–2444 (2002)

    Article  CAS  PubMed  Google Scholar 

  • Ding YB, Tang YY, Zhu WH, Xie YS. Fluorescent and colorimetric ion probes based on conjugated oligopyrroles. Chem. Soc. Rev. 44: 1101–1112 (2015)

    Article  CAS  PubMed  Google Scholar 

  • Ding YB, Zhu WH, Xie YS. Development of ion chemosensors based on porphyrin analogues. Chem. Rev. 117: 2203–2256 (2016)

    Article  CAS  PubMed  Google Scholar 

  • Gu X, Liu C, Zhu YC, Zhu YZ. A boron-dipyrromethene-based fluorescent probe for colorimetric and ratiometric detection of sulfite. J. Agric. Food Chem. 59: 11935–11939 (2011)

    Article  CAS  PubMed  Google Scholar 

  • Hassan SS, Hamza MS, Mohamed AH. A novel spectrophotometric method for batch and flow injection determination of sulfite in beverages. Anal. Chim. Acta 570: 232–239 (2006)

    Article  CAS  PubMed  Google Scholar 

  • He L, Lin W, Xu Q, Wei H. A unique type of pyrrole-based cyanine fluoropHores with turn-on and ratiometric fluorescence signals at different pH regions for sensing pH in enzymes and living cells. ACS Appl. Mater. Inter. 6: 22326–22333 (2014)

    Article  CAS  Google Scholar 

  • Leontiev AV, Rudkevich DM. Revisiting noncovalent SO2– amine chemistry: an indicator-displacement assay for colorimetric detection of SO2. J. Am. Chem. Soc. 127: 14126–14127 (2005)

    Article  CAS  PubMed  Google Scholar 

  • Li H. Rapidly responsive and highly selective fluorescent probe for sulfite detection in real samples and living cells. Anal. Chim. Acta 897: 102–108 (2015)

    Article  CAS  PubMed  Google Scholar 

  • Liu XJ, Yang QW, Chen WQ, Mo LN, Chen S, Kang J, Song XZ. A ratiometric fluorescent probe for rapid, sensitive and selective detection of sulfur dioxide with large Stokes shifts by single wavelength excitation. Org. Biomol. Chem. 13: 8663–8668 (2015)

    Article  CAS  PubMed  Google Scholar 

  • Lu CH, Bhattacharjee B, Hsu CH, Chen SY, Ruaan RC, Chang WH. Highly luminescent CdSe nanoparticles embedded in silica thin films. J. Electroceram. 17: 21–29 (2006)

    Article  CAS  Google Scholar 

  • McFeeters RF. Use and removal of sulfite by conversion to sulfate in the preservation of salt-free cucumbers. J. Food Prot. 61: 885–890 (1998)

    Article  CAS  PubMed  Google Scholar 

  • McFeeters RF, Barish AO. Sulfite analysis of fruits and vegetables by highperformance liquid chromatography (HPLC) with ultraviolet spectrophotometric detection. J. Agric. Food Chem. 51: 1513–1517 (2003)

    Article  CAS  PubMed  Google Scholar 

  • Peng MJ, Yang XF, Yin B, Guo Y, Suzenet F, En D, Duan YW. A hybrid coumarin–thiazole fluorescent sensor for selective detection of bisulfite anions in vivo and in real samples. Chem-Asian J. 9: 1817–1822 (2014)

    Article  CAS  PubMed  Google Scholar 

  • Santos-Figueroa LE, Giménez C, Agostini A, Aznar E, Marcos MD, Sancenón F, Amorós P. Selective and sensitive chromofluorogenic detection of the sulfite anion in water using hydropHobic hybrid organic–inorganic silica nanoparticles. Angew. Chem. Int. Ed. 52: 13712–13716 (2013)

    Article  CAS  Google Scholar 

  • Sun Q, Zhang W, Qian J. A ratiometric fluorescence probe for selective detection of sulfite and its application in realistic samples. Talanta 162: 107–113 (2017)

    Article  CAS  PubMed  Google Scholar 

  • Sun Y, Fan S, Zhang S, Zhao D, Duan L, Li R. A fluorescent turn-on probe based on benzo [e] indolium for bisulfite through 1, 4-addition reaction. Sens. Actuators B 193: 173–177 (2014a)

    Article  CAS  Google Scholar 

  • Sun Y, Zhao D, Fan S, Duan L, Li R. Ratiometric fluorescent probe for rapid detection of bisulfite through 1, 4-addition reaction in aqueous solution. J. Agric. Food Chem. 62: 3405–3409 (2014b)

    Article  CAS  PubMed  Google Scholar 

  • Sun Y, Zhong C, Gong R, Mu H, Fu E. A ratiometric fluorescent chemodosimeter with selective recognition for sulfite in aqueous solution. J. Org. Chem. 74: 7943–7946 (2009)

    Article  CAS  PubMed  Google Scholar 

  • Sun YQ, Liu J, Zhang J, Yang T, Guo W. Fluorescent probe for biological gas SO2 derivatives bisulfite and sulfite. Chem. Commun. 49: 2637–2639 (2013)

    Article  CAS  Google Scholar 

  • Sun YQ, Wang P, Liu J, Zhang J, Guo W. A fluorescent turn-on probe for bisulfite based on hydrogen bond-inhibited C [double bond, length as m-dash] N isomerization mechanism. Analyst 137: 3430–3433 (2012)

    Article  CAS  PubMed  Google Scholar 

  • Tan L, Lin W, Zhu S, Yuan L, Zheng K. A coumarin-quinolinium-based fluorescent probe for ratiometric sensing of sulfite in living cells. Org. Biomol. Chem. 12: 4637–4643 (2014)

    Article  CAS  PubMed  Google Scholar 

  • Tian H, Qian J, Sun Q, Bai H, Zhang W. Colorimetric and ratiometric fluorescent detection of sulfite in water via cationic surfactant-promoted addition of sulfite to α, β-unsaturated ketone. Anal. Chim. Acta. 788: 165–170 (2013)

    Article  CAS  PubMed  Google Scholar 

  • Wang JL, Hao YF, Wang H, Yang SX, Tian HY, Sun BG, Liu YG. Rapidly responsive and highly selective fluorescent probe for bisulfite detection in food. J. Agric. Food Chem. 65: 2883–2887 (2017)

    Article  CAS  PubMed  Google Scholar 

  • Wang H, Wu XM, Yang SX, Tian HY, Liu YG, Sun BG. A dual-site fluorescent probe for separate detection of hydrogen sulfide and bisulfite. Dyes Pigments 160: 757–764 (2019)

    Article  CAS  Google Scholar 

  • Wu MY, He T, Li K, Wu MB, Huang Z, Yu XQ. A real-time colorimetric and ratiometric fluorescent probe for sulfite. Analyst 138: 3018–3025 (2013)

    Article  CAS  PubMed  Google Scholar 

  • Wu MY, Li K, Li CY, Hou JT, Yu XQ. A water-soluble near-infrared probe for colorimetric and ratiometric sensing of SO2 derivatives in living cells. Chem. Commun. 50: 183–185 (2014)

    Article  CAS  Google Scholar 

  • Ye Z, Duan C, Sheng R, Xu J, Wang H, Zeng L. A novel colorimetric and ratiometric fluorescent probe for visualizing SO2 derivatives in environment and living cells. Talanta 176: 389–396 (2018)

    Article  CAS  PubMed  Google Scholar 

  • Yilmaz ÜT, Somer G. Determination of trace sulfite by direct and indirect methods using differential pulse polarography. Anal. Chim. Acta 603: 30–35 (2007)

    Article  CAS  PubMed  Google Scholar 

  • Yu C, Luo M, Zeng F, Wu S. A fast-responding fluorescent turn-on sensor for sensitive and selective detection of sulfite anions. Anal. Methods 4: 2638–2640 (2012)

    Article  CAS  Google Scholar 

  • Yuan L, Lin W, Zheng K, He L, Huang W. Far-red to near infrared analyte-responsive fluorescent probes based on organic fluorophore platforms for fluorescence imaging. Chem. Soc. Rev. 42: 622–661 (2013)

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

The programme was recognitioned by the Support Project of High-level Teachers in Beijing Municipal Universities in the Period of 13th Five-year Plan (CIT&TCD201804021); Scientific and technological innovation and service capacity building-basic research business funding-study on the flavor of typical Chinese traditional dishes (PXM2018-014213-000033).

Author information

Authors and Affiliations

  1. Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key laboratory of Flavor Chemistry, Beijing Technology and Business University, No. 11 Fucheng Road, Haidian District, Beijing, 100048, People’s Republic of China

    Haitao Chen, Xiaoming Wu, Jialin Wang, Hao Wang, Shaoxiang Yang, Hongyu Tian, Yongguo Liu & Baoguo Sun

  2. Research and Development Centre, China Tobacco Sichuan Industrial Co., Ltd., Chengdu, 610066, Sichuan, People’s Republic of China

    Feiyan Tao

Authors
  1. Haitao Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xiaoming Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jialin Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hao Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Feiyan Tao
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Shaoxiang Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Hongyu Tian
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Yongguo Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Baoguo Sun
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Shaoxiang Yang.

Ethics declarations

Conflict interest

All authors declare no conflict of interest.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 15681 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Chen, H., Wu, X., Wang, J. et al. A fluorescent probe for colorimetric detection of bisulfite and application in sugar and red wine. Food Sci Biotechnol 28, 983–990 (2019). https://doi.org/10.1007/s10068-019-00571-2

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10068-019-00571-2

Keywords

Search

Navigation